Asymmetric synthesis of peptides

C - Chemistry – Metallurgy – 07 – K

Patent

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Details

C07K 1/107 (2006.01) C07D 265/32 (2006.01) C07K 1/00 (2006.01) C07K 1/02 (2006.01) C07K 5/08 (2006.01)

Patent

CA 2622173

The present invention provides a process comprising substitution of an acceptor molecule comprising a group -XC(O)- wherein X is O, S or NR8, where R8 is C1-6 alkyl, C6-12 aryl or hydrogen, with a nucleophile, wherein the acceptor molecule is cyclised such that said nucleophilic substitution at -XC (O)- occurs without racemisation. This process has particular application for the production of a peptide by extension from the activated carboxy-terminus of an acyl amino acid residue without epimerisation.

La présente invention fournit un procédé comprenant la substitution d'une molécule d~accepteur comprenant un groupe -XC(O)- où X représente O, S ou NR8, où R8 représente un groupe alkyle en C1 à C6, un groupe aryle en C6 à C12 ou un atome d~hydrogène, par un nucléophile, la molécule d'accepteur étant cyclisée de telle sorte que ladite substitution nucléophile au niveau de -XC(O)- se produise sans racémisation. Ce procédé a une application particulière pour la production d'un peptide par extension à partir de la terminaison carboxy activée d'un résidu acide acylaminé sans épimérisation.

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